Dimethyl Sulfoxide → (3Rs,4r)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol

HRID 379969Notes

Reaction equation

HRID 379969 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][C@@H:7]([CH3:10])[CH2:8][OH:9])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[CH:30])[CH:24]=1>C(N(CC)CC)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][C@H:7]([CH3:10])[CH:8]([OH:9])[C:30]#[C:29][C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 1860033-EthynylpyridineHCID 57234620(S)-2-(4-Bromophenoxy)propan-1-ol

Product 1

HCID 53929738(3Rs,4r)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Prepared according to the method described in Example 1c) from (2S)-2-(4-bromophenoxy)propan-1-ol (9.24 g, Example 4b)), oxalyl chloride (4.38 ml), dimethyl sulfoxide (4.4 ml), triethylamine (22.4 ml), 3-pyridylacetylene (6.3 g) andn-butyllithium (2.5M in hexanes, 24 ml) to give the sub-title compound as an oil and as a 4:1 mixture of diastereomers (8.31 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f104d797307548d3a742e707f2e022d9
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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